Kinetic Study of 5-Hydroxymethylfurfural Synthesis from Fructose in High Pressure CO2-Water Two-Phase System

被引:20
作者
Labauze, Helene [1 ,2 ]
Camy, Severine [1 ]
Floquet, Pascal [1 ]
Benjelloun-Mlayah, Bouchra [2 ]
Condoret, Jean-Stephane [1 ]
机构
[1] Univ Toulouse, CNRS, UPS, INP,Lab Genie Chim,UMR 5503, 4 Allee Emile Monso, F-31030 Toulouse, France
[2] CIMV, 109 Rue Jean Barth,Diapason A, F-31670 Labege, France
关键词
CARBON-DIOXIDE; LEVULINIC ACID; DEHYDRATION; CONVERSION; GLUCOSE; WATER;
D O I
10.1021/acs.iecr.8b04694
中图分类号
TQ [化学工业];
学科分类号
0817 ;
摘要
In this work, synthesis of 5-hydroxymethylfurfural (5-HMF) from lignocellulosic biomass derived hexoses, fructose in our case, was developed in two-phase supercritical CO2-water systems. Conditions of reactions were above 10 MPa and 120 degrees C, i.e., the two-phase reacting mixture can be regarded as a subcritical water-supercritical CO2 system. From kinetic experiments and their modeling, it was possible to assess the effect of CO2 as a potential reversible acid catalyst. The kinetic model developed in this study considers also the catalytic contribution of acid byproducts, as proton providers, for the reaction of dehydration of fructose into 5-HMF. Selectivity toward S-HMF was improved with increasing pressure to reach a maximum of 80 mol % after 3 h of reaction at 150 degrees C and under 25 MPa of CO2, as only 60% was achieved without the use of pressurized CO2.
引用
收藏
页码:92 / 100
页数:9
相关论文
共 28 条
[1]   Heterogeneous acid-catalysts for the production of furan-derived compounds (furfural and hydroxymethylfurfural) from renewable carbohydrates: A review [J].
Agirrezabal-Telleria, I. ;
Gandarias, I. ;
Arias, P. L. .
CATALYSIS TODAY, 2014, 234 :42-58
[2]   Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides [J].
Chheda, Juben N. ;
Roman-Leshkov, Yuriy ;
Dumesic, James A. .
GREEN CHEMISTRY, 2007, 9 (04) :342-350
[3]   Experimental and Kinetic Modeling Studies on the Sulfuric Acid Catalyzed Conversion of D-Fructose to 5-Hydroxymethylfurfural and Levulinic Acid in Water [J].
Fachri, Boy A. ;
Abdilla, Ria M. ;
van de Bovenkamp, Henk H. ;
Rasrendra, Carolus B. ;
Heeres, Hero J. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2015, 3 (12) :3024-3034
[4]   PRODUCTION OF 5-HYDROXYMETHYLFURFURAL (HMF) VIA FRUCTOSE DEHYDRATION: EFFECT OF SOLVENT AND SALTING-OUT [J].
Gomes, F. N. D. C. ;
Pereira, L. R. ;
Ribeiro, N. F. P. ;
Souza, M. M. V. M. .
BRAZILIAN JOURNAL OF CHEMICAL ENGINEERING, 2015, 32 (01) :119-126
[5]   Thermodynamic model for biomass processing in pressure intensified technologies [J].
Gonzalez Prieto, Mariana ;
Sanchez, Francisco A. ;
Pereda, Selva .
JOURNAL OF SUPERCRITICAL FLUIDS, 2015, 96 :53-67
[6]   Acid-catalyzed reactions in carbon dioxide-enriched high-temperature liquid water [J].
Hunter, SE ;
Savage, PE .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2003, 42 (02) :290-294
[7]   Solubility of 5-Hydroxymethylfurfural in Supercritical Carbon Dioxide with and without Ethanol as Cosolvent at (314.1 to 343.2) K [J].
Jing, Yan ;
Hou, Yucui ;
Wu, Weize ;
Liu, Weina ;
Zhang, Baogang .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2011, 56 (02) :298-302
[8]   Temperature dependence of dissociation constants for formic acid and 2,6-dinitrophenol in aqueous solutions up to 175 degrees C [J].
Kim, MH ;
Kim, CS ;
Lee, HW ;
Kim, K .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1996, 92 (24) :4951-4956
[9]   Fractionation of aqueous isopropanol mixtures in a countercurrent packed column using supercritical CO2 [J].
Lalam, R. ;
Chamali, S. ;
Camy, S. ;
Rouzineau, D. ;
Kessas, R. ;
Condoret, J. -S. .
JOURNAL OF SUPERCRITICAL FLUIDS, 2015, 101 :24-35
[10]  
Lee R, 2016, GREEN CHEM, V18, P5118, DOI [10.1039/c6gc01697a, 10.1039/C6GC01697A]